9-(9Z-hexadecenoyloxy)-octadecanoate

Three steps

• 1,2-di-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + 9-hydroxy-octadecanoate = 9-(9Z-octadecenoyloxy)-octadecanoate + 2,3-di-(9Z)-octadecenoyl-sn-glycerol
  3. 9-hydroxy-octadecanoate + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 9-(9Z-octadecenoyloxy)-octadecanoate + 2-(9Z-octadecenoyl)-glycerol

  Catalysed by CEL, ADTRP, AIG1, PNPLA2One of 3 routes

• 1,2,3-tri-(9Z-octadecenoyl)-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + 9-hydroxy-octadecanoate = 9-(9Z-octadecenoyloxy)-octadecanoate + 2,3-di-(9Z)-octadecenoyl-sn-glycerol
  3. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + 9-hydroxy-octadecanoate = 9-(9Z-octadecenoyloxy)-octadecanoate + 2,3-di-(9Z)-octadecenoyl-sn-glycerol

  Catalysed by CEL, ADTRP, AIG1, PNPLA2One of 3 routes

• butanoyl-CoAReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. Utilized Transport
  3. transport of butyryl-CoA and L-carnitine (cytosol to mitochondria)

  Catalysed by CEL, ADTRP, AIG1, SLC33A1 and 2 moreendoplasmic reticulum, cytosol, mitochondrial matrixOne of 2 routes

• hexadecanoyl-CoAReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. hexadecanoyl-CoA + 2 Fe(II)-[cytochrome b5] + O2 + 2 H(+) = (9Z)-hexadecenoyl-CoA + 2 Fe(III)-[cytochrome b5] + 2 H2O

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 9 morecytosolOne of 2 routes

• octanoyl-CoAReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. Beta Oxidation Fatty Acid

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 9 morecytosol, mitochondrial matrixOne of 2 routes

• O-acetyl-(R)-carnitineReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. Utilized Transport
  3. Acetyl-CoA:carnitine O-acetyltransferase

  Catalysed by CEL, ADTRP, AIG1, CPT1A and 2 moreendoplasmic reticulum, cytosolOne of 9 routes

• an acyl-CoAReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. acyl-CoA pool formation and breakdown

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 7 morecytosol

• (5Z,8Z,11Z,14Z,17Z)-eicosapentaenoateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, ADTRP, AIG1cytosol, extracellular spaceOne of 12 routes

• (8Z,11Z,14Z)-eicosatrienoateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, ADTRP, AIG1cytosol, extracellular spaceOne of 13 routes

• 1-hexadecanoyl-2-[(9Z)-hexadec-9-enoyl]-sn-glycero-3-phosphateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. 1-hexadecanoyl-sn-glycero-3-phosphate + (9Z)-hexadecenoyl-CoA = 1-hexadecanoyl-2-[(9Z)-hexadec-9-enoyl]-sn-glycero-3-phosphate + CoA

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 8 morecytosol

• 1-hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphoethanolamineReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. 1-hexadecanoyl-sn-glycero-3-phosphoethanolamine + (9Z)-hexadecenoyl-CoA = 1-hexadecanoyl-2-(9Z)-hexadecenoyl-sn-glycero-3-phosphoethanolamine + CoA

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 8 morecytosol

• 1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholineReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + 1-hexadecanoyl-sn-glycero-3-phosphocholine = 1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine + CoA

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 9 morecytosol

• 1-(9Z-octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + 1-(9Z-octadecenoyl)-sn-glycero-3-phosphate = 1-(9Z-octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphate + CoA

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 8 morecytosol

• 1-(9Z-octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-L-serineReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. 1-(9Z-octadecenoyl)-sn-glycero-3-phospho-L-serine + (9Z)-hexadecenoyl-CoA = 1-(9Z-octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-L-serine + CoA

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 8 morecytosol

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 9-hydroxy-octadecanoate + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 9-(9Z-octadecenoyloxy)-octadecanoate + 2-(9Z-octadecenoyl)-glycerol
  3. 2-(9Z-octadecenoyl)-glycerol + hexadecanoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + CoA

  Catalysed by CEL, ADTRP, AIG1, PNPLA2 and 4 more

• 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 9-hydroxy-octadecanoate + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 9-(9Z-octadecenoyloxy)-octadecanoate + 2-(9Z-octadecenoyl)-glycerol
  3. 1-octadecanoyl-2-(9Z-octadecenoyl)-sn-glycerol + H2O = 2-(9Z-octadecenoyl)-glycerol + octadecanoate + H(+)

  Catalysed by CEL, ADTRP, AIG1, PNPLA2 and 1 more

• 1-dodecanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 9-hydroxy-octadecanoate + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 9-(9Z-octadecenoyloxy)-octadecanoate + 2-(9Z-octadecenoyl)-glycerol
  3. 2-(9Z-octadecenoyl)-glycerol + dodecanoyl-CoA = 1-dodecanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by CEL, ADTRP, AIG1, PNPLA2 and 2 more

• 1-tetradecanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 9-hydroxy-octadecanoate + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 9-(9Z-octadecenoyloxy)-octadecanoate + 2-(9Z-octadecenoyl)-glycerol
  3. 2-(9Z-octadecenoyl)-glycerol + tetradecanoyl-CoA = 1-tetradecanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by CEL, ADTRP, AIG1, PNPLA2 and 2 more

• 1-hexadecanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 9-hydroxy-octadecanoate + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 9-(9Z-octadecenoyloxy)-octadecanoate + 2-(9Z-octadecenoyl)-glycerol
  3. 2-(9Z-octadecenoyl)-glycerol + hexadecanoyl-CoA = 1-hexadecanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by CEL, ADTRP, AIG1, PNPLA2 and 2 more

• 1-octadecanoyl-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 9-hydroxy-octadecanoate + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 9-(9Z-octadecenoyloxy)-octadecanoate + 2-(9Z-octadecenoyl)-glycerol
  3. 2-(9Z-octadecenoyl)-glycerol + octadecanoyl-CoA = 1-octadecanoyl-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by CEL, ADTRP, AIG1, PNPLA2 and 2 more

• 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 9-hydroxy-octadecanoate + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 9-(9Z-octadecenoyloxy)-octadecanoate + 2-(9Z-octadecenoyl)-glycerol
  3. 2-(9Z-octadecenoyl)-glycerol + (5Z,8Z,11Z,14Z)-eicosatetraenoyl-CoA = 1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by CEL, ADTRP, AIG1, PNPLA2 and 2 more

• 1-(9Z,12Z-octadecadienoyl)-2-(9Z-octadecenoyl)-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 9-hydroxy-octadecanoate + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 9-(9Z-octadecenoyloxy)-octadecanoate + 2-(9Z-octadecenoyl)-glycerol
  3. 2-(9Z-octadecenoyl)-glycerol + (9Z,12Z)-octadecadienoyl-CoA = 1-(9Z,12Z-octadecadienoyl)-2-(9Z-octadecenoyl)-glycerol + CoA

  Catalysed by CEL, ADTRP, AIG1, PNPLA2 and 2 more

• hexadecyl (9Z)-hexadecenoateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. hexadecan-1-ol + (9Z)-hexadecenoyl-CoA = hexadecyl (9Z)-hexadecenoate + CoA

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 9 morecytosol

• 1,2,3-tri-(9Z,12Z)-octadecadienoylglycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 1,2,3-tri-(9Z,12Z)-octadecadienoylglycerol + 9-hydroxy-octadecanoate = 2,3-di-(9Z,12Z)-octadecadienoyl-sn-glycerol + 9-(9Z,12Z-octadecadienoyloxy)-octadecanoate
  3. 1,2,3-tri-(9Z,12Z)-octadecadienoylglycerol + 9-hydroxy-octadecanoate = 2,3-di-(9Z,12Z)-octadecadienoyl-sn-glycerol + 9-(9Z,12Z-octadecadienoyloxy)-octadecanoate

  Catalysed by CEL, ADTRP, AIG1, PNPLA2One of 2 routes

• 1-hexadecanoyl-2,3-di-(9Z)-octadecenoyl-sn-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + 9-hydroxy-octadecanoate = 9-(9Z-octadecenoyloxy)-octadecanoate + 2,3-di-(9Z)-octadecenoyl-sn-glycerol
  3. 1-hexadecanoyl-2,3-di-(9Z)-octadecenoyl-sn-glycerol + 9-hydroxy-octadecanoate = 1-hexadecanoyl-3-(9Z)-octadecenoyl-sn-glycerol + 9-(9Z-octadecenoyloxy)-octadecanoate

  Catalysed by CEL, ADTRP, AIG1, PNPLA2One of 4 routes

• 3-(9Z-octadecenoyl)-sn-glycerolReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 1,2,3-tri-(9Z-octadecenoyl)-glycerol + 9-hydroxy-octadecanoate = 9-(9Z-octadecenoyloxy)-octadecanoate + 2,3-di-(9Z)-octadecenoyl-sn-glycerol
  3. 2,3-di-(9Z)-octadecenoyl-sn-glycerol + H2O = 3-(9Z-octadecenoyl)-sn-glycerol + (9Z)-octadecenoate + H(+)

  Catalysed by CEL, ADTRP, AIG1, PNPLA2 and 1 more

• 3-oxo-(11Z)-octadecenoyl-CoAReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + malonyl-CoA + H(+) = 3-oxo-(11Z)-octadecenoyl-CoA + CO2 + CoA

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 9 morecytosol

• O-dodecanoyl-R-carnitineReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. Utilized Transport
  3. carnitine O-palmitoyltransferase (dodecanoylcarnitine)

  Catalysed by CEL, ADTRP, AIG1, CPT1A and 2 moreendoplasmic reticulum, cytosolOne of 7 routes

• (11Z,14Z)-eicosadienoateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, ADTRP, AIG1cytosol, extracellular spaceOne of 12 routes

• (17Z)-hexacosenoateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, ADTRP, AIG1cytosol, extracellular spaceOne of 12 routes

• (7Z,10Z,13Z,16Z,19Z)-docosapentaenoateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, ADTRP, AIG1cytosol, extracellular spaceOne of 12 routes

• (7Z,10Z,13Z,16Z)-docosatetraenoateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, ADTRP, AIG1cytosol, extracellular spaceOne of 12 routes

• (2E,9Z)-hexadecadienoyl-CoAReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. medium-chain acyl-CoA dehydrogenase (palmitoleoyl-CoA)

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 11 morecytosol, mitochondrial matrixOne of 3 routes

• 2-(9Z-octadecenoyl)-sn-glycero-3-phosphateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 9-hydroxy-octadecanoate + 1,2-di-(9Z-octadecenoyl)-sn-glycerol = 9-(9Z-octadecenoyloxy)-octadecanoate + 2-(9Z-octadecenoyl)-glycerol
  3. 2-(9Z-octadecenoyl)-glycerol + ATP = 2-(9Z-octadecenoyl)-sn-glycero-3-phosphate + ADP + H(+)

  Catalysed by CEL, ADTRP, AIG1, PNPLA2 and 1 more

• (5Z,8Z,11Z)-eicosatrienoateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, ADTRP, AIG1cytosol, extracellular spaceOne of 12 routes

• hexadecanoateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. 1-hexadecanoyl-2,3-di-(9Z)-octadecenoyl-sn-glycerol + 9-hydroxy-octadecanoate = 9-hexadecanoyloxy-octadecanoate + 2,3-di-(9Z)-octadecenoyl-sn-glycerol
  3. 9-hexadecanoyloxy-octadecanoate + H2O = 9-hydroxy-octadecanoate + hexadecanoate + H(+)

  Catalysed by CEL, ADTRP, AIG1, PNPLA2

• tricosanoateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. (10Z)-heptadecenoic acid formation
  3. (10Z)-heptadecenoic acid formation

  Catalysed by CEL, ADTRP, AIG1cytosol, extracellular spaceOne of 12 routes

• cholesteryl (9Z)-hexadecenoateReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. long-chain-fatty-acid-CoA ligase (palmitolate)
  3. (9Z)-hexadecenoyl-CoA + cholesterol = cholesteryl (9Z)-hexadecenoate + CoA

  Catalysed by CEL, ADTRP, AIG1, SLC27A2 and 8 morecytosol

• O-4,8-dimethylnonanoyl-(R)-carnitineReach from here →
  1. 9-(9Z-hexadecenoyloxy)-octadecanoate + H2O = (9Z)-hexadecenoate + 9-hydroxy-octadecanoate + H(+)
  2. Utilized Transport
  3. Carnitine Dimethyl Nonanoyl Transferase, Revsible, Peroxisomal

  Catalysed by CEL, ADTRP, AIG1, CRAT and 1 moreendoplasmic reticulum, cytosol, peroxisomeOne of 5 routes